US4746707A - Process for the selective hydrogenation of unsaturated compounds - Google Patents
Process for the selective hydrogenation of unsaturated compounds Download PDFInfo
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- US4746707A US4746707A US06/891,618 US89161886A US4746707A US 4746707 A US4746707 A US 4746707A US 89161886 A US89161886 A US 89161886A US 4746707 A US4746707 A US 4746707A
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08C—TREATMENT OR CHEMICAL MODIFICATION OF RUBBERS
- C08C19/00—Chemical modification of rubber
- C08C19/02—Hydrogenation
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/04—Reduction, e.g. hydrogenation
Definitions
- This invention relates to a process for the selective hydrogenation of unsaturated, optionally high molecular weight, compounds carrying reducible groups containing nitrogen.
- CC-double bonds may be selectively hydrogenated on solid catalysts in the presence of reducible groups containing nitrogen. Palladium or platinum catalysts are used for this purpose and yields of up to 90% are obtained (Houben Weyl, Methoden der Organischen Chemie, Volume IV, 1c, Redutechnisch I (1980), page 168). The selectivity is, however, in many cases unsatisfactory. Thus, only 31% of the desired 1-cyanocyclohexane is obtained when platinum oxide is used for the hydrogenation of 1-cyanocyclohexene. (See M. Freifelder, Practical Catalytic Hydrogenation, (1971), page 157).
- phosphane-containing complexes of the type L n MX 2 (L represents CO or tertiary phosphine; n represents 3 or 4; M represents ruthenium or osmium; and X represents halogen and/or hydrogen) may be used for the hydrogenation of keto, formyl, nitrile, non-aromatic --C ⁇ C-- and --C.tbd.C-- groups, these complexes invariably hydrogenating all the groups of this type present.
- Hydridocarboxylato-tris-triphenyl phosphaneruthenium complexes have a catalytic activity for the hydrogenation of 1-olefins (J. Chem. Soc. (A) 1969, pages 2610-2615), but they fail to hydrogenate olefins which are substituted or have non-terminally situated olefinic bonds. This is presumably due to steric hindrance by the triphenyl phosphane ligands which prevent transfer of hydride.
- RuH(CF 3 CO 2 )(PPh 3 ) 3 may also be used as catalyst for the partial hydrogenation of conjugated dienes (Litvin, E. F.; Freidlin, L. Kh. and Karinov, K. G.; in Neftkhimiya 12 (1972) 3, 318-323).
- DE-OS No. 2,539,132 postulates a solvent-dependent selective hydrogenation of butadiene-acrylonitrile copolymers with the aid of the known rhodium catalyst which preserves the CN-triple bonds and cis-double bonds and hydrogenates the vinylic and trans-double bonds quantitatively if chlorobenzene is used as solvent. If other solvents are used, in particular ketones, only low degrees of hydrogenation are achieved.
- the homogeneous or, preferably, heterogeneous hydrogenation of unsaturated polyhydroxy hydrocarbons having molecular weights of up to 4,000 with the aid of ruthenium catalysts with preservation of the hydroxyl groups is disclosed in DE-OS No. 2,459,115. It is stated there that aliphatic hydrocarbons, aromatic hydrocarbons, alcohols, ethers, esters and water may be used as solvents for heterogeneous hydrogenation, but no corresponding statements are made for homogeneous hydrogenation. It is said that the polymers may also contain, for example, acrylonitrile as comonomer; no detailed descriptions are given, but it may be remembered that it is known from U.S. Pat. No. 3,454,644, Example IX, that the nitrile group of benzonitrile is hydrogenated to the amino group by homogeneous ruthenium catalysis in ethanol.
- This problem may surprisingly be solved by a homogeneous reaction using ruthenium carboxylate complexes.
- the present invention thus relates to the homogeneous hydrogenation of unsaturated compounds carrying reducible groups containing nitrogen with preservation of the reducible groups containing nitrogen, characterised in that the catalyst used is a compound corresponding to the following general formula:
- R 1 represents optionally substituted alkyl, aryl, cycloalkyl or aralkyl
- L represents a phosphane or arsane
- n 0 or 1
- n 1 or 2;
- p 2 or 3.
- the alkyl groups may be, for example, straight- or branched-chain saturated hydrocarbon groups having from 1 to 20, preferably from 1 to 12, most preferably from 1 to 6, carbon atoms.
- the cyclo-alkyl groups may consist, for example, of cyclic, saturated hydrocarbon groups having from 5 to 7 carbon atoms.
- Suitable aryl groups include aromatic hydrocarbon groups of the benzene series having from 6 to 18, preferably from 6 to 10, carbon atoms.
- aralkyl groups include aryl-substituted alkyl groups consisting in their aliphatic moiety of a straight or branched-chain hydrocarbon group having from 1 to 6 carbon atoms and in the aromatic moiety of a group of the benzene series, preferably phenyl.
- alkyl, cycloalkyl, aryl and aralkyl groups described above may be substituted with hydroxyl, C 1 -C 6 alkoxy, C 1 -C 6 carbalkoxy, fluorine, chlorine or di-C 1 -C 4 -alkylamino, and the cycloalkyl, aryl and aralkyl groups may in addition be substituted by C 1 -C 6 alkyl groups, and the alkyl, cycloalkyl and aralkyl groups may contain keto groups.
- groups R 1 include methyl, ethyl, propyl, isopropyl, tertiary butyl, cyclohexyl, phenyl, benzyl and trifluoromethyl.
- Methyl, ethyl and tertiary butyl are preferred groups R 1 .
- ligands L include those corresponding to the following general formulae: ##STR1## wherein R 2 , R 3 and R 4 which may be the same or different, conform to the definition for R 1 .
- ligands L triphenyl phosphane, diethylphenyl phosphane, tritolyl phosphane, trinaphthyl phosphane, diphenyl methyl phosphane, diphenyl butyl phosphane, tris-(p-carbomethoxy phenyl)phosphane, tris-(p-cyanophenyl)-phosphane, tributyl phosphane, tris-(trimethoxy phenyl)-phosphanes, bis-(trimethylphenyl)-phenyl phosphanes, bis-(trimethoxy phenyl)-phenyl phosphanes, trimethyl phenyl diphenyl phosphanes, trimethoxyphenyl diphenyl phosphanes, bis-(dimethylphenyl)-phenyl phosphanes, tris-(
- Triaryl phosphanes are preferred, in particular triphenyl phosphane.
- Some of the complexes used are known. They may be prepared, for example, directly from hydrated ruthenium trichloride in the presence of an excess of the ligand L and of the sodium salt of the corresponding carboxylic acid or from the corresponding complex RuCl 2 L 3 with the sodium salt of a carboxylic acid (R. W. Mitchell, A. Spencer and G. Wilkinson in J. C. S. Dalton 1973, page 852). Other methods of preparation are described by D. Rose, J. D. Gilbert, R. P. Richardson and G. Wilkinson in J. Chem. Soc. (A) 1969, page 2914, 2915 and A. Dobson, S. D. Robinson and M. F. Uttley in J. C. S. Dalton 1975, page 376.
- unsaturated compounds carrying reducible groups containing nitrogen include nitriles, imines and oximes, nitriles being preferred.
- the high molecular weight, unsaturated compounds carrying reducible groups containing nitrogen are preferably copolymers containing nitrile groups obtained from 85 to 50%, by weight, preferably from 82 to 55%, by weight, of at least one conjugated diene, from 15 to 50%, by weight, preferably from 18 to 45%, by weight, of at least one unsaturated nitrile and from 0 to 10%, by weight, preferably from 0 to 8%, by weight, of at least one other monomer capable of being copolymerised with conjugated dienes and unsaturated nitriles.
- conjugated dienes examples include butadiene-(1,3), 2-methyl-butadiene-(1,3), 2,3-dimethyl butadiene-(1,3) and pentadiene-(1,3).
- Acrylonitrile and methacrylonitrile are suitable unsaturated nitriles.
- the monomers used may also be aromatic vinyl compounds, such as styrene, o-, m- or p-methyl styrene, ethyl styrene, vinyl naphthalene or vinyl pyridine, ⁇ , ⁇ -unsaturated monocarboxylic acids containing from 3 to 5 carbon atoms, such as acrylic acid, methacrylic acid or crotonic acid, or ⁇ , ⁇ -unsaturated dicarboxylic acids containing 4 or 5 carbon atoms, such as maleic, fumaric, citraconic or itaconic acid, or vinyl chloride, vinylidene chloride, N-methylol acrylamide or vinyl alkyl ethers having from 1 to 4 carbon atoms in the alkyl moiety.
- aromatic vinyl compounds such as styrene, o-, m- or p-methyl styrene, ethyl styrene, vinyl naphthalene or vinyl pyridine
- the compound hydrogenated is preferably a binary copolymer of butadiene and acyrlonitrile.
- the molecular weight of the polymer is not critical and is generally in the region of from 500 to 500,00 g/mol, preferably from 1,000 to 200,000 g/mol, more preferably from 30,000 to 150,000 g/mol (numerical average determined by gel permeation chromatography).
- the conversion rates or degrees of hydrogenation may amount to as much as 100%, but hydrogenation may be stopped at an earlier stage if necessary.
- the polymers obtained by the process according to the present invention preferably have degrees of hydrogenation of over 80%, in particular above 90%, especially above 95%, most preferably above 99%.
- Hydrogenation may be carried out solvent-free, especially if the process is carried out on low molecular weight, liquid compounds, or it may be carried out in solution.
- Suitable solvents for hydrogenation include in particular low molecular weight ketones having from 3 to 10 carbon atoms, such as acetone, butanone, pentanones, cyclopentanone, cyclohexanone and acetophenone.
- the concentration of unsaturated compound, based on the whole homogeneous phase, should be at least 1, and is preferably from 5 to 40%, by weight.
- the concentration of catalyst (calculated as ruthenium) based on the unsaturated compound generally amounts to from 10 to 1,000, preferably from 40 to 600, ppm.
- Hydrogenation is suitably carried out at from 80° to 200° C., preferably from 100° to 180° C., in particular from 115° to 160° C., and under a hydrogen pressure of from 1 to 350 bar, preferably from 20 to 250 bar.
- the catalyst may be removed by the conventional methods after the reaction and the product may be purified, e.g. by distillation or crystallization.
- the polymer is removed from the solution by the conventional methods, such as evaporation, injection of steam or the addition of non-solvent. This is followed by drying to remove any residues of solvent or water.
- the polymer solutions obtained by the process according to the present invention may easily be worked-up by the injection of steam to recover the solid polymer without forming deposits on the stripper wall, stirrer or screen and also that no mechanical cleaning of the stripper is required after the product has been worked-up.
- the polymers which have been hydrogenated according to the present invention may be cured by peroxide or sulphur vulcanisation in the conventional manner unless vulcanisation is carried out by a process of cross-linking by irradiation.
- the low molecular weight compounds carrying reducible groups containing nitrogen and hydrogenated according to the present invention are valuable intermediate products for the preparation of active substances.
- the conversion rate was 100%. No amines could be detected.
- the conversion rate was 77%. No hydrogenation products of the oxime group could be detected.
- Example 1 was repeated with 300 ppm of Ru in the form of Ru(CH 3 CO 2 ) 2 (PPh 3 ) 2 .
- the degree of hydrogenation was more than 99% after 3 hours.
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- Chemical & Material Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
RuH.sub.m (R.sub.1 CO.sub.2).sub.n (L).sub.p
Description
RuH.sub.m (R.sub.1 CO.sub.2).sub.n (L).sub.p
TABLE 1 ______________________________________ Catalyst RuH(RCO.sub.2)(PPh.sub. 3).sub.3 200 ppm Example No. 2 3 4 5 6 R: CH.sub.3 CH.sub.2 (CH.sub.3).sub.3 C C.sub.6 H.sub.5 C.sub.6 H.sub.5 CH.sub.2 CF.sub.3 ______________________________________ Degree of 99.7 99.6 98.1 99.0 97.8 (%) hydrogenation ______________________________________
Claims (8)
RuH.sub.m (R.sub.1 CO.sub.2).sub.n (L).sub.p
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19853529252 DE3529252A1 (en) | 1985-08-16 | 1985-08-16 | METHOD FOR SELECTIVE HYDRATION OF UNSATURATED COMPOUNDS |
DE3529252 | 1985-08-16 |
Publications (1)
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US4746707A true US4746707A (en) | 1988-05-24 |
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US06/891,618 Expired - Lifetime US4746707A (en) | 1985-08-16 | 1986-08-01 | Process for the selective hydrogenation of unsaturated compounds |
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US (1) | US4746707A (en) |
EP (1) | EP0213422B1 (en) |
JP (1) | JPS6242937A (en) |
CA (1) | CA1274544A (en) |
DE (2) | DE3529252A1 (en) |
Cited By (62)
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US4925900A (en) * | 1988-09-16 | 1990-05-15 | Polysar Limited | Halogenated-hydrogenated acrylonitrile-butadiene rubber |
US4978771A (en) * | 1985-11-19 | 1990-12-18 | Bayer Aktiengesellschaft | Process for the selective hydrogenation of unsatuated compounds |
US5034469A (en) * | 1989-06-29 | 1991-07-23 | Bayer Aktiengesellschaft | Hydrogenation of unsaturated polymers containing nitrile groups |
US5272202A (en) * | 1988-12-29 | 1993-12-21 | Nippon Zeon Co., Ltd. | Hydrogenation process of unsaturated, nitrile-group-containing polymer and aqueous emulsion of hydrogenated polymer |
USRE34548E (en) * | 1985-11-19 | 1994-02-15 | Bayer Aktiengesellschaft | Process for the selective hydrogenation of unsaturated compounds |
US5430163A (en) * | 1990-07-19 | 1995-07-04 | Dsm Copolymer | Palladium catalyst systems for selective hydrogenation of dienes |
US5556919A (en) * | 1994-09-30 | 1996-09-17 | Nippon Zeon Co., Ltd. | Rubber composition comprising nitrile group-containing highly saturated copolymer rubber and ethylenically saturated copolymer rubber |
US5561197A (en) * | 1995-06-27 | 1996-10-01 | University Of Waterloo | Hydrogenation of diene copolymers |
US5651995A (en) * | 1994-09-30 | 1997-07-29 | Nippon Zeon Co., Ltd. | Highly saturated nitrile rubber, process for producing same, vulcanizable rubber composition, aqueous emulsion and adhesive composition |
US5683819A (en) * | 1994-09-30 | 1997-11-04 | Nippon Zeon Co., Ltd. | Composite of highly saturated nitrile rubber with fiber, and belt composed thereof |
DE4106466C2 (en) * | 1990-03-01 | 1999-11-04 | Nippon Zeon Co | Process for the hydrogenation of unsaturated copolymers containing nitrile groups |
US6084033A (en) * | 1997-05-08 | 2000-07-04 | Nantex Industry Co., Ltd. | Bimetallic complex catalyst systems, their preparations and application in the hydrogenation of unsaturated copolymers |
WO2002066419A1 (en) * | 2001-02-21 | 2002-08-29 | Ube Industries, Ltd. | Process for producing 2-halogenocycloalkanone oxime |
US6602962B2 (en) | 2000-12-22 | 2003-08-05 | Bayer Inc. | Process for the production of hydrogenated nitrile rubber |
US20030171518A1 (en) * | 2000-06-07 | 2003-09-11 | Hans Magg | Branched copolymers based on unsaturated nitriles and on conjugated dienes |
US6673881B2 (en) | 2001-06-12 | 2004-01-06 | Bayer Inc. | Process for the preparation of low molecular weight hydrogenated nitrile rubber |
US20040097660A1 (en) * | 2000-08-25 | 2004-05-20 | Harald Bender | Hydrogenated nitrile rubbers with improved low-temperature properties |
US20070049699A1 (en) * | 2005-07-14 | 2007-03-01 | Lanxess Inc. | Process for the preparation of low mooney nitrile terpolymers |
US20070049700A1 (en) * | 2005-08-30 | 2007-03-01 | Werner Obrecht | Method for the degradation of nitrile rubber by metathesis in the presence of ruthenium- or osmium-based catalysts |
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US5651995A (en) * | 1994-09-30 | 1997-07-29 | Nippon Zeon Co., Ltd. | Highly saturated nitrile rubber, process for producing same, vulcanizable rubber composition, aqueous emulsion and adhesive composition |
US5683819A (en) * | 1994-09-30 | 1997-11-04 | Nippon Zeon Co., Ltd. | Composite of highly saturated nitrile rubber with fiber, and belt composed thereof |
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US6084033A (en) * | 1997-05-08 | 2000-07-04 | Nantex Industry Co., Ltd. | Bimetallic complex catalyst systems, their preparations and application in the hydrogenation of unsaturated copolymers |
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Also Published As
Publication number | Publication date |
---|---|
EP0213422A2 (en) | 1987-03-11 |
DE3669162D1 (en) | 1990-04-05 |
JPS6242937A (en) | 1987-02-24 |
CA1274544A (en) | 1990-09-25 |
JPH0317812B2 (en) | 1991-03-11 |
EP0213422A3 (en) | 1988-01-27 |
EP0213422B1 (en) | 1990-02-28 |
DE3529252A1 (en) | 1987-02-19 |
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